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Substituted isoxazoles as fungicides

Inactive Publication Date: 2006-04-06
SYNGENTA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0079] 4. Technical materials. The compounds and combinations of the present invention may also be used in the area of controlling fungal infection (particularly by mold and mildew) of technical materials, including protecting technical material against attack of fungi and reducing or eradicating fungal infection of technical materials after such infection has occurred. Technical materials include but are not limited to organic and inorganic materials wood, paper, leather, natural and synthetic fibers, composites thereof such as particle board, plywood, wall-board and the like, woven and non-woven fabrics, construction surfaces and materials, cooling and heating system surfaces and materials, ventilation and air conditioning system surfaces and materials, and the like. The compounds and combinations according to the present invention can be applied to such materials or surfaces in an amount effective to inhibit or prevent disadvantageous effects such as decay, discoloration or mold in like manner as described above. Structures and dwellings constructed using or incorporating technical materials in which such compounds or combinations have been applied are likewise protected against attack by fungi.

Problems solved by technology

However, some fungi can produce disease in plants, humans and / or animals.
In fact, some crops cannot be grown usefully without the use of fungicides.
However, the treatment of fungal infestations and infections continues to be a major problem.
Furthermore, fungicide and antifungal drug resistance has become a serious problem, rendering these agents ineffective for some agricultural and therapeutic uses.

Method used

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  • Substituted isoxazoles as fungicides
  • Substituted isoxazoles as fungicides
  • Substituted isoxazoles as fungicides

Examples

Experimental program
Comparison scheme
Effect test

example 1

3-(2,6-Dichlorophenyl)-4-[(3-pyridyl) hydroxymethyl]-5-trimethylsilylisoxazole (Compound 1) and 3-(2,6-dichlorophenyl)-5-[(3-pyridyl) hydroxymethyl]-4-trimethylsilylisoxazole (Compound 2)

[0095] A mixture of 55 mg (0.24 mmol) of 2,6-dichloro-N-hydroxybenzenecarboximidoyl chloride, 50 mg (0.24 mmol) of 1-(3-pyridyl)-3-trimethylsilyl-2-propyn-1-ol, and 20 mg (0.24 mmol) of sodium bicarbonate in 2 mL of isopropyl alcohol was heated at 55° C. for 24 hrs. The reaction mixture was diluted with ether. The ether layer was washed with saturated sodium chloride solution, and was dried over magnesium sulfate. The drying agent was filtered off, and the ether was removed by rotoevaporation. The crude product was purified by preparative thin layer chromatography (prep TLC), and two products were isolated. The less polar product (10 mg, 0.025 mmol) was identified as 3-(2,6-dichlorophenyl)-4-[(3-pyridyl)hydroxy-methyl]-5-trimethylsilylisoxazole. 1H NMR (CDCl3): δ 0.45 (br s, 9), 5.82 (s, 1), and 7....

example 2

5-(3-Chlorophenyl)-3-(2,4-dichlorophenyl)-4-[(3-pyridyl)hydroxymethyl]isoxazole (Compound 4)

[0097] A mixture of 53 mg (0.24 mmol) of 2,4-dichloro-N-hydroxybenzenecarboximidoyl chloride, 50 mg (0.21 mmol) of 1-(3-pyridyl)-3-(3-chlorophenyl)-2-propyn-1-ol, and 26 mg (0.31 mmol) of sodium bicarbonate in 2.5 mL of isopropyl alcohol was heated at 55° C. on a rotary table shaker equipped with a heated sand bath. After 20 hrs, an additional 20 mg of 2,4-dichloro-N-hydroxybenzenecarboximidoyl chloride and 10 mg of sodium bicarbonate was added, and the reaction mixture was stirred and heated for another 16 hrs. The mixture was then diluted with ether, and the solution was washed with saturated sodium chloride and dried over magnesium sulfate. The drying agent was filtered off, and the ether was removed by rotoevaporation. The crude product was purified by prep TLC to give 15 mg (0.035 mmol) of 5-(3-chlorophenyl)-3-(2,4-dichlorophenyl)-4-[(3-pyridyl)hydroxymethyl]isoxazole. 1H NMR (CDCl3): δ...

example 3

5-(3-Chlorophenyl)-3-(2,4-dichlorophenyl)-4-[(3-pyridyl)acetoxymethyl]isoxazole

[0098] To a solution of 43 mg (0.10 mmol) of 5-(3-chlorophenyl)-3-(2,4-dichlorophenyl)-4-[(3-pyridyl)hydroxymethyl]isoxazole in 2 mL of pyridine was added 19 μL (0.20 mmol) of acetic anhydride. The reaction was stirred overnight at room temperature, and then the pyridine was removed under vacuum. The residue was taken up in ethyl acetate, washed with saturated sodium chloride, and the ethyl acetate fraction dried over magnesium sulfate. The drying agent was filtered off, and the ethyl acetate was removed by rotoevaporation. The crude product was purified by preparative thin layer chromatography (prep TLC) to give 35 mg (0.074 mmol) of 5-(3-chlorophenyl)-3-(2,4-dichlorophenyl)-4-[(3-pyridyl)acetoxymethyl]isoxazole.

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Abstract

The present invention provides compounds of formula I: along with methods of making the same, compostions thereof, and methods of use thereof, particularly methods of use as fungicides.

Description

RELATED APPLICATIONS [0001] This application claims the benefit of U.S. Provisional Patent Application Ser. No. 60 / 608,589, filed Sep. 10, 2004, the disclosure of which is incorporated by reference herein in its entirety.FIELD OF THE INVENTION [0002] The present invention concerns substituted isoxazoles, compositions thereof, and methods of use thereof for the control of microbial pests, particularly fungal pests, on plants. BACKGROUND OF THE INVENTION [0003] The incidence of serious fungal infections, either systemic or topical, continues to increase for plants, animals, and humans. Many fungi are common in the environment and not harmful to plants or mammals. However, some fungi can produce disease in plants, humans and / or animals. [0004] Fungicides are compounds, of natural or synthetic origin, which act to protect plants against damage caused by fungi, including oomycetes. Current methods of agriculture rely heavily on the use of fungicides. In fact, some crops cannot be grown u...

Claims

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Application Information

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IPC IPC(8): A01N25/26A01N43/40A01N43/80C07D413/02C07D261/06
CPCA01N43/80C07D261/08C07D413/06
Inventor LEE, SHY-FUHGLIEDT, MICAH
Owner SYNGENTA LTD